Sodium hydride → HCID 86716194, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(pyrimidin-5-yl)acetonitrile (1.8 g, 15.1 mmol) in DMF (20 mL) was degassed and (bromomethyl)cyclopropane was added (2.04 g, 15.1 mmol). The reaction mixture was cooled to −10° C., NaH was added (720 mg, 18.1 mmol, 60% in mineral oil) in portions under N2 and stirred at the same temperature for 45 mins. The reaction mixture was quenched with sat. NH4Cl and extracted with EtOAc (30 ml×3). The organic layer was washed with brine, dried over Na2SO4 and concentrated. The crude product was purification by column chromatography on silica gel (petroleum ether: EtOAc=3:1) to give 3-cyclopropyl-2-(pyrimidin-5-yl)propanenitrile (2.25 g, yield: 85%).1H NMR (CDCl3 400 MHz): δ9.22 (s, 1H), 68.78 (s, 2H), 3.80 (t, J=8 Hz, 2H), 1.98-1.92 (m, 1H), 1.83-1.79 (m, 1H), 0.87-0.83 (m, 1H), 0.61-0.59 (m, 2H), 0.21-0.13 (m, 2H).

Provenance & Evidence